C₆₀H₉₂O₉Si₃

Base Information

• Chemical Name: C₆₀H₉₂O₉Si₃
• CAS No.: 1289512-92-0
• Molecular Formula: C₆₀H₉₂O₉Si₃
• Molecular Weight: 1041.64
• Mol file: 1289512-92-0.mol

Synonyms:

Chemical Property of C₆₀H₉₂O₉Si₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₆₀H₉₂O₉Si₃

There total 5 articles about C₆₀H₉₂O₉Si₃ which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 52.0%

(7S,8S)-9-[(tert-butyldiphenylsilyl)oxy]-7-hydroxy-8-methylnon-1-en-3-one (1289512-72-6) + (1S,2R)-1-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-1-[(tert-butyldimethylsilyl)oxy]but-3-en-2-ol (1289512-65-7) → C60H92O9Si3 (1289512-92-0)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; In dichloromethane; for 20h; Inert atmosphere; Reflux;

DOI:10.1002/ejoc.201001411

Reference yield:

(1S,3R,5S)-1-benzyloxymethyl-3-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-5-methyl-2,8-dioxa-bicyclo[3.2.1]octane (1063713-63-2) → C60H92O9Si3 (1289512-92-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine hydrogenfluoride / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.13 h / -50 - -30 °C / Inert atmosphere

2.2: 0.75 h / -30 °C / Inert atmosphere

2.3: 0.17 h / -30 °C / Inert atmosphere

3.1: tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 20 h / Inert atmosphere; Reflux

With Hoveyda-Grubbs catalyst second generation; oxalyl dichloride; pyridine hydrogenfluoride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 2.1: Swern oxidation / 2.2: Swern oxidation / 2.3: Swern oxidation;

DOI:10.1002/ejoc.201001411

Reference yield:

(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]ethanol (1289512-61-3) → C60H92O9Si3 (1289512-92-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.13 h / -50 - -30 °C / Inert atmosphere

1.2: 0.75 h / -30 °C / Inert atmosphere

1.3: 0.17 h / -30 °C / Inert atmosphere

2.1: tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 20 h / Inert atmosphere; Reflux

With Hoveyda-Grubbs catalyst second generation; oxalyl dichloride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation / 1.2: Swern oxidation / 1.3: Swern oxidation;

DOI:10.1002/ejoc.201001411

upstream raw materials:

(1S,3R,5S)-1-benzyloxymethyl-3-[(2R,3R,5R)-5-[(S)-1,2-bis-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-tetrahydro-furan-2-yl]-5-methyl-2,8-dioxa-bicyclo[3.2.1]octane

(7S,8S)-9-[(tert-butyldiphenylsilyl)oxy]-7-hydroxy-8-methylnon-1-en-3-one

(1S,2R)-1-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-1-[(tert-butyldimethylsilyl)oxy]but-3-en-2-ol

(S)-2-((2R,4R,5R)-5-{(1S,3R,5S)-1-[(benzyloxy)methyl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-4-[(tert-butyldimethylsilyl)oxy]-2-methyltetrahydrofuran-2-yl)-2-[(tert-butyldimethylsilyl)oxy]ethanol